DAI HOC QUOC
GIA
HA
NOI
TRlrtTNG
DAI HOC KHOA HOC
TITNHIEN
• • •
•
Ten de tai
" TONG
HOP MOT SO HOP
CHnt HUU
CO
ft
CO
HOflT TINH SINH
HOC
MA
SO: QT-05- 19
OAl
HOC QUOC GIA HA
MOl
Oi
I
5fib
CHU
TRI
D£
TAI:
Th.S THAN THI

cuu ca'u
tao va thu hoat
tinh
sinh hoc
ctia m6t
so
dan xu^t
ciia axit arylacrylic. Trong do quan tarn han ca la t6ng hgp
m6t
s6' hidrazit cua
axit arylacrylic va
chuy^n
hoa thanh hidrazon
chiia nhan
5-nitrofuranyl
c6 hoat
tinh
sinh
hoc cao.
- Not dung: Tien hanh phan
vtng
t6ng hgp cac
ch^t
huu ca, xac dinh
c^u
tao san pham nha
cac
phuong
phap ph6
IR,

C^u
true
cua cac hgp
cha't
mod
nh^n
dugc da dugc xac
nh^n nhcy
cac phuong phap
phd
h6ng ngoai, ph6
c6ng hucmg ttf
hat
nhan
va ph6
kh6'i
lugng.
• Hoat
tinh
sinh hoc cua mot so san
phSm
dugc
thir
tren
mOt s6
chung
n&i
va vi
khu^n.
•

d6
tai la 10 trieu d6ng chu yeu dugc
dung de mua hoa chat nghiem. Mot
phSn
chu yeu khac dugc
diing
d^
thue
mucm
chuyen
mon va
lao
dong.
KHOA HOA HOC
Hd
not,
ngayi^
thdng
^
nam 2006
CHU
NHllM Dfi
TAI
"u-
PGS TS. Tran Thi
Nhu
Mai , . ThS. Tran
Thj
Thanh Van
S.

• The reaserching project has contributed to the graduations of one master.
PHAN
NOI
DUNG
CHINH
MUC LUC
Trang
A.
Ldl Md
DAU 4
B.
NOI
DUNG
CHINH 5
1.
Tdng
hgp cac metyl va etyl este ciia axit arylacrylic 5
2.
T6ng
hgp cac hidrazit cua axit arylacrylic 5
3.
T6ng hgp cac hidrazon cua axit arylacrylic 8
4.
Thir
hoat
tinh
sinh hoc cua mot
s6'
cha't
tdng hgp dugc

ca c6 hoat
tinh
sinh hoc"
vcd
mong muon gop mot
phin
nho cho muc
dich
tren. Trong
d6
tai chung t6i quan
tam
han ca den viec tdng hgp mot
s6
dan xuit
cia axit arylacrylic nhu cac este, hidrazit, hidrazon
chiia nhan
5-nitro furanyl da
dugc bie't la c6 hoat
tinh
sinh hoc cao.
Cac
cha't
tdng hgp dugc da dugc xac dinh
ca'u
tao bang cac phuong phap vat
ly
hien
dai va m5t
s6'

thu dugc
a
dang tinh
th^
hay dang long a dieu kien
thucmg,
c6 diem nong chay hoac diem
spi
xac
dinh.^
Ca^u true
cua san
phim
dugc xac dinh bang cac phuang phap phd hong ngoai,
tu ngoai, phd
cdng huong
tu nhan proton va phd kh6'i lugng.
Sa dd phan
utig:
R-CH=CH-COOH
+
R'-OH
^ "
R-CH=CH-COOR'
+ H2O
R:
C^H^-,
P-CH3O-C6H4-,
m-N02-C6H4-,
m-Cl-C6H4-

-QH3
*
nc
cnai)
(271)
93-94
125-126
53-54
(146-147)
91-92
Hieu
suat
79,4
74,6
74,1
81,9
72,6
63,8
Phd hong ngoai
(cm"^
Vc=o
1711
1711
1708
1732
1717
1706
Vc=C
1638
1639

277,5
216,5
260,3
203,0
272,4
220,8
303,0
Tren phd
hdng
ngoai cua cac metyl va etyl este
ciia
axit arylacrylic cho tha'y
cue
dai ha'p thu cua nhom -OH axit c6 chan rong
(tir
2313-2512 cm') da
m^t
han, thay vao do
la
sir
xua't hien cac
cue
dai hap thu ciia lien ke't
C-O-C
este
a
khoang 1200-1300 cm"' (xem
hinh 1 va 2).
2.
Tdng hgp cac hidrazit cua axit arylacrylic.

hat nhan proton. Ke't qua tdng hgp cac hidrazit dugc cho
a
bang 2.
San
ph^m
hidrazit tao thanh c6 phd
hdng
ngoai khac vdi cac este ban dau. Tren phd
hdng
ngoai xua't hien cac
cue
dai ha'p thu cua lien ket NH
a
vung
tir
3230-3416 cm"',
cue
dai
h^p
thu cua lien ket C=0
a
1664-1716 cm', nhung cac
cue
dai hap thu thuang tu,
khOng
sac net do c6 hien tugng tao lien ke't hidro giua nhom C=0 cacbonyl va
NH2.
Bang
2:
Ket qua tong hap vd xac dinh cdu tao

71,4
50,0
62,1
Pho hong ngoai
(cm')
Vc=0
1714
1716
1644
1692
1705
Vc=C
1636
1639
1664
1640
1642
Vc-N
1279
1202
1174
1207
1211
1175
1284
1242
VNOI
1532
1344
1511

-CH=CH-
cung xua't hien rat ro net va dac
biet la cac pic c6
cucmg
do ye'u 6 do chuyen dich hoa hoc 8,0 va 2,lppm dac
trung
cho
proton cua nhom
-NH-NH-
(xem bang 5).
Dai
hoc
Ouoc gia
turyi acrylalTTiRfyr
-^-r-r
n H-r.,.,.
Hinh 2: Pho hong ngoai cua metyl
3-furyl
acrylat.
96
94
92
90
m
B6
64
82
80
78
76

iJng
ngung tu cac hidrazit
vcd
furan-2 andehit the thu dugc cac
hidrazon khac nhau. Tren phd hong ngoai cua hidrazon
khOng
tha'y xua't hien dao dong
hoa tri
ciia
lien ke't N-H cua nhom
NH2
trong khoang 3416-3230
cm'
ma thay vao do la
lien ke't C-H cua vong furan
6
khoang 3199-3016
cm'
va C-O-C a
1348-1184
cm' va dac
biet
d viing
1684-1600
cm"'
xua't hien them nhieu dinh dan xen nhau, dieu do cho tha'y
lien ke't C=N da dugc
hinh
thanh (xem bang 3).
Bang 3: Ket qua tong hgp

228-
230
232-
234
228-
230
Hieu
suat
67,2
65,0
64,0
65,5
64,0
Phd
hong ngoai (cm'^)
Vc=0
1648
1678
1642
1684
1675
Vc=c
1623
1623
1603
—
1644
Vc=N
1662
1678

260,4
Phd kh6'i lugng cua cac hidrazon cho cac ion phan tu dung
vcd
du kien. Lien ket
0=C-NH-
ciia cac hidrazon kh6ng ben, de bi cat dut va nhung hidrazon
chiia
Cio trong
nguyen
tir
c6 xua't hien ion dong vi (xem so do phan manh).
CI
^O^CH=
o
II
CH-C-NH-N=CH
M""
319/321
'I
W
O'
NO-
NH-N=CH
m/e 139
O
o
NO2
C1-^Q^CH=CH-C-
m/e
165/167

•
i;
1">,N
c.^
^
Hinh 4.
Phd
hong ngoai cua 5-nitro
furiliden-m-nitro
xinamoyl hidrazon
Bang 4.
Phdkhdi luang
cua mot
so
chat tdng hgp
duac
CTPT
C9H9O5N
C.SHHOJNJ
C,4H,o04N3Cl
C,4Hn04N3
Khoi
luong
PT
211
270
319/321
285
m/e
(1%)

CH=CH-C-NH-NH2
5 (ppm)
6,66(d,
J=16Hz,
IH,
H'); 7,33(d, J=3,5Hz,
IH,
H');
6,75(d,
J=4Hz,
IH,
H^);
7,4(d,
J=16Hz,
IH,
H');
l,34(t,3H,
-CH3);
4,28(q,
2H,
-CH2)
6,8(d,
J=15,5Hz,
IH,
H');
7,81(d,
J=4Hz,
IH,
H');
7,5(d,

hidrazon. Ke't qua cho tha'y miu T2, T4, T7, T8 c6 tac dung doi vci chung S.A, S.B, P.A.
Cac mau
Tl
den T5 deu c6 tac dung vci na'm men. Dac biet miu T4 c6 tac dung vci ca 4
chung tren. Ke't qua thu hoat tinh sinh hoc
th^
hien a bang 6.
Chung S.A: Staphylococus Aureus (Tu
cSu
vang
thu6c
c^u
khuan gam
(+))
Chung P.A: Pseudomonas Aeraginosa
(Mii
xanh
thuCc true khudn
gam (-))
Chung B.A: Bacillus Subtilis
(ThuOc
gam (+))
Na'm men: Candida albicans
10
Bang 6: Ket qua thu hoat tinh sinh hoc cua mot
so
dan xudt cua axit arylacrylic.
Mhx
(50^1)
Tl

0
0
0
12
0
16
B.A
0
10
0
20
0
30
Nam
men
Co tac
dune
Co tac
dune
Co tac
dung
Co tac
dung
Co tac
dung
Khong
tac dung
5.
Thuc nghiem
Diem chay cua cac san

la'y
lap
dlu,
trung hoa
Icfp
d^u
bang
Na2C03,
lam
lanh
bang da
mu<5i.
Thu san pham va ket tinh lai trong
etanohnudc.
• Cac hidrazit cua axit arylacrylic dugc tdng hgp
true
tie'p tu cac este va
hidrazinhidrat.
ViTa khua^y
va dun
each
thuy
hCn
hgp phan tog trong 12
gicf.
ca't loai
bcft
etanol sau do dd
true
tiep

cot
tren he dung moi thich hgp.
2.
Xac dinh
c^u
tao ciia cac san pham ran bang phuang phap phd hong ngoai,
tir
ngoai,
phd cong huong
tir
hat nhan proton va phd khoi lugng.
3.
Mot
s6 cha't
duoc thu hoat tinh sinh hoc tren mot so chung vi
khu^n
va na'm.
C.TAI
LIEU THAM
KHAO
1.
American Medical Association (1994),
'Drug Eva/uarian
"chapter 73.
2.
Dimmock J.R., Taylor
U.G
(1984),
''Synthesis
and physical propeties of

Dinh
Trieu, Phan
Dinh
Long,
Trfo
Thi Thanh Van, Doan Manh Chat, Tran
Thi Phuong Thao
Tdng hgp, xac dinh ca'u tao va thir hoat tinh sinh hoc cua mot so dan xua't 5-aryl-2-
mecapto-1,3,4-oxadiazol.
Bao cao
6
Hoi nghi khoa hoc
Trucmg
Dai hoc Khoa hoc Tu
nhien,
tr. 129-133
2.
Nguyen
Dinh
Trieu, Doan buy Tien,
Trkn
Thi Thanh Van
Phd hdng ngoai
ciia
mot so fomazan
chu:a
di vong quinolin
Bao cao
6
Hoi nghi khoa hoc Truong Dai hoc Khoa hoc Tu nhien, tr.

di vong pirol va
4,5-dimetylthiazolyl
fomazan vdi mot so ion kim loai
chuyen
tie'p.
5.
Nguyen
Dinh
Trieu,
TrSn
Thi Thanh Van
^
Tinh
hang s6
b6n ciia phiic
fomazan
chura
di vong vdi
m6t
so ion kim loai chuyen
tiep
Tap
chi
Phan
tich
Ly Hoa Sinh, so 2, tap 10, tr. 31-36, 2005
6. Trdn Thi Thanh Van, Nguyen
Dinh
Trieu
Tdng hgp va nghien cuu ca'u tao mot so hgp cha't fomazan

Bai giri tap
chi
Hoa hoc va
ling
dung, se dang trong nam 2006
13
SCIENTIFIC PROJECT
BRANCH: Chemistry
PROJECT CATEGORY:
Fundemental
Project of Hanoi University of Science.
1.
Title
"Synthesis of some organic compounds have biological
activity''
2.
Code QT-05-19
3.
Managing Institution: Hanoi University of Science
4.
Implementing Institution: Faculty of Chemistry
5. Key implementors: - Tran Thi Thanh Van, M.A - Director
6. Duration: 12 months since
January,
2005.
1.
Budget: 10 millions VND
8. Main results:
- Results in science and technology
- Results in practical

so phufc
hgp chat huru ca c6 hoat tinh sinh
hoc"
Ma so: QT-
05-19
Co quan chu
tri
de tai (hoac du
an):
Khoa Hda-Trudng DHKHTN
Dja
chi:
19 Le Thanh Tong Ha noi
Tel:
04 8 533 503
Co quan quan ly de tai (hoac du
an):
Trudng
Dai hoc Khoa hoc Tu nhien
Dia chi: 334 Nguyen
Trai-
Thanh Xuan-Ha noi
Tel:
Tdng kinh
phi
thuc chi: 10 000 000 dong (Mudi trieu dong)
Trong do: -
Tuf
ngan sach Nha
nude:

Bao mat:
a. Phd bien rong rai:
0
b.
Phd bien han che:
D
c. Bao mat:
D
Tom tat ket qua nghien curu:
• Da nghien cuu phan
vcng
tdng hgp mot so metyl, etyl este, hidrazit, hidrazon
ciia
axit arylacrylic.
• ca'u true cua cac hgp chat mdi nhan dugc da dugc xac nhan nhd cac phuong phap
phd hong ngoai, phd cong huong tu hat nhan va phd khoi lugng.
• Mot so cha't tdng hgp dugc da dugc thir hoat
ti'nh
khang khuan, khang nam.
Kien nghi
v^qliT^^i^T^
ddi tugng ap dung nghien cuu;
Chu
nhieni
de tai
Thu truong
caquan
chu tn de tai
Chu
Ijch

HOC VA
ONIG
DUNG
So:
03 - 2006/GCN
CONG HOA
XA
HOI
CHU
NGHiA
VIET NAM
Doclap-Tudo-Hanhphuc
Hi) Noi.
ngay
07
thdng
03
lulm 200()
GIAY
CHONG
NHAN
Tap
chi
Hoa hoc va
U"ng
dung
chilng
nhan
bai
bao:

ARYLACRYLIC ' "^
SYNTHESISE, ESTABLISH STRUCTURE AND BIOACTIVITY OF
SOMF
DERIVATIVES OF ARYLACRYLIC ACID
^^^^ ^i
Thanh Van,
Nsuven
H^i
n^^
XT
^ ,
. . SUMMARY
syntheztT
00^0^
^T^^':^^^^:Z ^H
^r^^'^^"
^^ —^ of
spectroscopy.
The
bioactivity
of sorecomTnlrh I ^^"' ^^•' ^^ ^"'^ ^MR
been shown good inhibition
aiLsTsti,
'A'
" ''''"^- '^^'
°^
"^^''^ ^ave
Bacillus Subtms and Cand^^aalSs at
stgi""
"

R-CH=CH-COOR'
.
H^G
R:
QH5-,
P-CH3O-C6H4-,
m-N02-QH4-,
m-Cl-QH4-
R
-^QHs-,
CH3-
Hnn ^^*^^" "^f ^^^^
^°^
^^
P''^"
"^S ^'"^ ^^^'" ^^
^^"^f^
^^?"
tirong
doi
dl
dang
Chune
toi
dung du ancol de tang hieu
sua't
phan ung este hoa. Ket qua tdng hap cac este duac cho
6
Tong hop cac hidrazit cua axit arylacrylic.
Cac hidrazit

hieu cua proton trong nhom
-CH=CH-
cung xua't hien ra't ro net va
d'
biet la
cac pic cd cudng do yeu d do chuyen dich hda hoc 8,0 va 2
I ppm
dac
fnm
i!*^
proton cua nhom -NH-NH- (xem bang 4). '
^^"^
•
'
™^
^^°
Bang 1: Ket qud
tSng
hap
vd
xac dinh cdu tao cdc este
cda
axit
arylacryll
TT R
C^<
R'
-QH
(T»,)
P-CH3O-QH4-

74,1
81,9
1708
1638
1206
1173
1732 1715
(146-147)
91-92
72,6
63,8
1717
1706
1323
1295
'CI
Pho
tu
ngoai
(^iiia>.
nm)
1641
1640
1318
1258^
1017
1211
1524
1355
277,5

'
nc
24-25
85-86
103-105
23-24
120-121
Hieu
suat
55,5
58,5
71,4
50,0
62,1
Pho
hong ngoai (cm'i
Vc=o
1714
1716
1644
1692
1705
Vc=r
1636
1639
1664
1640
1642
VCN
1279

Tong hgp cac hidrazon cua axit arylacrylic,
Thirc
hien phan
ling ngimg
tu cac hidrazit vdi furan-2 andehit the thu
dirac
cac
nidrazon
khac nhau. Tren ph6 hdng ngoai cua hidrazon khong tha'y xua't hien dao dong
,
["
'"^''^" ^^^ ^"" '"^ "''""^ ^2
trong khoang 3416-3230 cm' ma thay vao do
ll
lien
ket C-H cua vong furan d khoang 3199-3016 cm' va C-O-C d
1348-1184
cm' va dac
biet
a
viing
1684-1600 cm' xua't hien them nhieu
dinh
dan xen nhau,
didu
do cho tha'v
lien
ket
C=N
da dugc hinh thanh (xem bang 3).

H
Ar-CH=CH-C-NH-N=CH-/~\-
-yO
224-
225
Hieu
suat
198-
200
67,2
Vc=0
Ph6ji6ngngoai(cm')
1648
228-
230
65,0
CHC___VC=N
1623
1662
1678
232-
/J4
64.0
65.5
1623
1678
1642
228-
230
64,0

277,0
221,8
376,6
281,0
214,8
324.0
228,0
204,0
380,8
323,4
316,8
260,4
te-N=CH-
'' ^
O
m/e 139
O
NO2
C1^^^CH=CH-C-
o
NO
m/e 165/167
<^CHECH
m/e 125
^
m/e 103
So dd phan manh cua 5-nitro fufuryliden p-clo xinamoyl hidrazon
^ang
4: Pho cong huong tic hat nhdn proton cua mot
so

2H,
-CH,)
6,8(d,
J=15,5Hz,
IH,
H'); 7,81(d, J=4Hz
IH,
H^);
7,5(d,
J=2Hz,
IH,
H^);
7,55(d,
J=15,5Hz,
IH,
H^);
8,0(q,J-l,0Hz,
IH,
H^)-
6£(dJ=2,0Hz,2H,
H')
3
Thu hoat
tinh
sinh hoc cua mot so chat tong hgp dugc.
Tien
hanh
thur
hoat
tinh

" ' ^ ^° ^^^ '^'^"g ^oi
ca 4
S P A ••
^*"P^/°'^°'^"^
.A"'-^"^
(Tu
c^u
vang thugc
cSu khu&
gam
(+))
Chung RA: Pseudomonas Aeraginosa (Mu xanh thuoc
true
khua'n gam
(
Chung B.A: Bacillus Subtilis (Thuoc gam (+))
' ' '^'"'"^ Sam
(-))
Nam
men: Candida albicans
Bdng
5:
Ket qud thi hoat
Unh
sinh hoc cua mot so ddn xudt cua axit arylacryhc.
Miu
(50(il)
Tl
T2
13

0
0
12
0
16
B.A
0
10
0
20
0
30
Nam
mpn
Cd tac
1 duno
1
^\'"f^
Co tac
1
dun?
Co lac
dung
Co tac
dung
Co lac
dung
Khong
tac dung
J

da
muoi. Thu san
ph^'m
va ket tinh lai trong
etanol:nudc.
» Cac hidrazit cua axit arylacrylic dugc tong hgp
true
tiep tu cac este va
hidrazinhidrat.
Vijra khu^'y
va dun
each
thuy
h6n
hgp phan ung trong
12
gia.
Cat
loai bdt
etanol sau do dd
true
tiep h6n hgp vao coc
nude
da, lam lanh
v6
0-5"C.
Ket tinh lai trong etanol.
• Cac hidrazon duac tdng hgp
b^ng
each

N^l.
3.
Stephen Gillespie (2004),
"Medical
Microbiology
illustrated",
Butterworth
Heinemnn.
4.
Kirrk Othmer (1994), "Encyclopedia of Chemical
technology',
John. Wiley and
sons,
NewYork, Vol.13,
3'^
ed.